Bromine → 2-Bromo-2'-fluoroacetophenone

HRID 2194678Notes

Reaction equation

HRID 2194678 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[Br:11]Br>C(O)(=O)C>[Br:11][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 96744o-Fluoroacetophenone

Product 1

HCID 27374492-Bromo-2'-fluoroacetophenoneYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-(2-fluorophenyl)ethanone (15.1 g) in acetic acid (150 mL) was added bromine (5.8 mL). The mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield 22.9 g, yield 97%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92167c2185df4506aeb219f7a7a5b0f0
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

Loading…